메뉴 건너뛰기




Volumn 46, Issue 9, 2011, Pages 3810-3819

Isomalyngamide A, A-1 and their analogs suppress cancer cell migration in vitro

Author keywords

Antimetastatic agents; Cancer cell migration; Integrin signaling; Isomalyngamide; Marine metabolites; Sialyltransferase inhibitor

Indexed keywords

1 ACETYL 4 METHOXY 1H PYRROL 2(5H)ONE; 2 [2,2 DIMETHYL 3 OXO 3 (2 TETRADECANAMIDOETHYLAMINO)PROPANAMIDO]ACETIC ACID; 2,2,5,5 TETRAMETHYL 1,3 DIOXANE 4,6 DIONE; 3 (2 TERT BUTOXY 2 OXOETHYLAMINO) 2,2 DIMETHYL 3 OXOPROPANOIC ACID; 4 METHOXY 1 TETRADECANOYL 1H PYRROL 2(5H)ONE; ANTINEOPLASTIC AGENT; BETA1 INTEGRIN; FOCAL ADHESION KINASE; ISOMALYNGAMIDE A; ISOMALYNGAMIDE A 1; ISOMALYNGAMIDE A DERIVATIVE; METHYL 3 (4 METHOXY 2 OXO 2,5 DIHYDRO 1H PYRROL 1 YL) 3 OXOPROPANOATE; N (2 AMINOETHYL)PIVALAMIDE; N (2 AMINOETHYL)TETRADECANAMIDE; N [2 [3 (2,4 DIOXOPYRROLIDIN 1 YL) 2,2 DIMETHYL 3 OXOPROPANAMIDO]ETHYL]TETRA DECANAMIDE; PROTEIN KINASE B; TERT BUTYL 2 [2,2 DIMETHYL 3 OXO 3 (2 TETRADECANAMIDOETHYLAMINO)PROPANAMIDO]ACETATE; UNCLASSIFIED DRUG;

EID: 80052917694     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.05.049     Document Type: Article
Times cited : (56)

References (48)
  • 1
    • 57149132404 scopus 로고    scopus 로고
    • Synthesis of marine natural products with antimalarial activity
    • I. Mancini, G. Guella, and A. Defant Synthesis of marine natural products with antimalarial activity Mini-Rev. Med. Chem. 8 2008 1265 1284
    • (2008) Mini-Rev. Med. Chem. , vol.8 , pp. 1265-1284
    • Mancini, I.1    Guella, G.2    Defant, A.3
  • 2
    • 33750508517 scopus 로고    scopus 로고
    • Antiplasmodial marine natural products in the perspective of current chemotherapy and prevention of malaria: A review
    • D. Laurent, and F. Pietra Antiplasmodial marine natural products in the perspective of current chemotherapy and prevention of malaria: a review Mar Biotechnol. 8 2006 433 447
    • (2006) Mar Biotechnol. , vol.8 , pp. 433-447
    • Laurent, D.1    Pietra, F.2
  • 3
    • 0242299243 scopus 로고    scopus 로고
    • First enantiospecific total synthesis of the antitubercular marine natural product pseudopteroxazole. Revision of assigned stereochemistry
    • J.P. Davidson, and E.J. Corey First enantiospecific total synthesis of the antitubercular marine natural product pseudopteroxazole. Revision of assigned stereochemistry J. Am. Chem. Soc. 125 2003 13486 13489
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 13486-13489
    • Davidson, J.P.1    Corey, E.J.2
  • 5
    • 42249112437 scopus 로고    scopus 로고
    • Total synthesis and structure assignment of papuamide B, A potent marine cyclodepsipeptide with anti-HIV properties
    • W. Xie, D. Ding, W. Zi, G. Li, and D. Ma Total synthesis and structure assignment of papuamide B, A potent marine cyclodepsipeptide with anti-HIV properties Angew. Chem. Int. Ed. 47 2008 2844 2848
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 2844-2848
    • Xie, W.1    Ding, D.2    Zi, W.3    Li, G.4    Ma, D.5
  • 6
    • 34547395751 scopus 로고    scopus 로고
    • Bis and tris indole alkaloids from marine organisms: New leads for drug discovery
    • L. Gupta, A. Talwar, and P.M. Chauhan Bis and tris indole alkaloids from marine organisms: new leads for drug discovery Curr. Med. Chem. 14 2007 1789 1803
    • (2007) Curr. Med. Chem. , vol.14 , pp. 1789-1803
    • Gupta, L.1    Talwar, A.2    Chauhan, P.M.3
  • 7
    • 2342449312 scopus 로고    scopus 로고
    • Natural products with anti-HIV activity from marine organisms
    • L.A. Tziveleka, C. Vagias, and V. Roussis Natural products with anti-HIV activity from marine organisms Curr. Top. Med. Chem. 3 2003 1512 1535
    • (2003) Curr. Top. Med. Chem. , vol.3 , pp. 1512-1535
    • Tziveleka, L.A.1    Vagias, C.2    Roussis, V.3
  • 8
    • 66349117644 scopus 로고    scopus 로고
    • Chasing the treasures of the sea-bacterial marine natural products
    • T.A. Gulder, and B.S. Moore Chasing the treasures of the sea-bacterial marine natural products Curr. Opin. Microbiol. 12 2009 252 260
    • (2009) Curr. Opin. Microbiol. , vol.12 , pp. 252-260
    • Gulder, T.A.1    Moore, B.S.2
  • 10
    • 38749120651 scopus 로고    scopus 로고
    • Lamellarins and related pyrrole-derived alkaloids from marine organisms
    • H. Fan, J. Peng, M.T. Hamann, and J.F. Hu Lamellarins and related pyrrole-derived alkaloids from marine organisms Chem. Rev. 108 2008 264 284
    • (2008) Chem. Rev. , vol.108 , pp. 264-284
    • Fan, H.1    Peng, J.2    Hamann, M.T.3    Hu, J.F.4
  • 11
    • 77649184218 scopus 로고    scopus 로고
    • Bioactive natural products (Part N)
    • A. Rahman, Elsevier Science Ltd. Amsterdam
    • Y. Kimura Bioactive natural products (Part N) A. Rahman, In the Studies in Natural Products Chemistry 34 2008 Elsevier Science Ltd. Amsterdam 35 76
    • (2008) In the Studies in Natural Products Chemistry , vol.34 , pp. 35-76
    • Kimura, Y.1
  • 12
    • 34248574507 scopus 로고    scopus 로고
    • Chemistry and biology in search of antimetastatic agents
    • L. Perez, and S.J. Danishefsky Chemistry and biology in search of antimetastatic agents ACS Chem. Biol. 20 2007 159 162
    • (2007) ACS Chem. Biol. , vol.20 , pp. 159-162
    • Perez, L.1    Danishefsky, S.J.2
  • 13
    • 77951116071 scopus 로고    scopus 로고
    • Migrastatin analogues target fascin to block tumor metastasis
    • L. Chen, S. Yang, J. Jakoncic, J.J. Zhang, and X.Y. Huang Migrastatin analogues target fascin to block tumor metastasis Nature 464 2010 1062 1066
    • (2010) Nature , vol.464 , pp. 1062-1066
    • Chen, L.1    Yang, S.2    Jakoncic, J.3    Zhang, J.J.4    Huang, X.Y.5
  • 14
    • 77949343941 scopus 로고    scopus 로고
    • Diverted total synthesis leads to the generation of promising cell-migration inhibitors for treatment of tumor metastasis: In vivo and mechanistic studies on the migrastatin core ether analog
    • T. Oskarsson, P. Nagorny, I.J. Krauss, L. Perez, M. Mandal, G. Yang, O. Ouerfelli, D. Xiao, M.A. Moore, J. Massagué, and S.J. Danishefsky Diverted total synthesis leads to the generation of promising cell-migration inhibitors for treatment of tumor metastasis: in vivo and mechanistic studies on the migrastatin core ether analog J. Am. Chem. Soc. 132 2010 3224 3228
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 3224-3228
    • Oskarsson, T.1    Nagorny, P.2    Krauss, I.J.3    Perez, L.4    Mandal, M.5    Yang, G.6    Ouerfelli, O.7    Xiao, D.8    Moore, M.A.9    Massagué, J.10    Danishefsky, S.J.11
  • 15
    • 63149086762 scopus 로고    scopus 로고
    • Lactimidomycin, iso-migrastatin and related glutarimide-containing 12-membered macrolides are extremely potent inhibitors of cell migration
    • J. Ju, S.R. Rajski, S.K. Lim, J.W. Seo, N.R. Peters, F.M. Hoffmann, and B. Shen Lactimidomycin, iso-migrastatin and related glutarimide-containing 12-membered macrolides are extremely potent inhibitors of cell migration J. Am. Chem. Soc. 131 2009 1370 1371
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 1370-1371
    • Ju, J.1    Rajski, S.R.2    Lim, S.K.3    Seo, J.W.4    Peters, N.R.5    Hoffmann, F.M.6    Shen, B.7
  • 16
    • 55249098380 scopus 로고    scopus 로고
    • Evaluation of new migrastatin and dorrigocin congeners unveils cell migration inhibitors with dramatically improved potency
    • J. Ju, S.R. Rajski, S.K. Lim, J.W. Seo, N.R. Peters, F.M. Hoffmann, and B. Shen Evaluation of new migrastatin and dorrigocin congeners unveils cell migration inhibitors with dramatically improved potency Bioorg. Med. Chem. Lett. 18 2008 5951 5954
    • (2008) Bioorg. Med. Chem. Lett. , vol.18 , pp. 5951-5954
    • Ju, J.1    Rajski, S.R.2    Lim, S.K.3    Seo, J.W.4    Peters, N.R.5    Hoffmann, F.M.6    Shen, B.7
  • 17
  • 19
    • 0942265463 scopus 로고    scopus 로고
    • Discovery of potent cell migration inhibitors through total synthesis: Lessons from structure-activity studies of (+)-migrastatin
    • J.T. Njardarson, C. Gaul, D. Shan, X.Y. Huang, and S.J. Danishefsky Discovery of potent cell migration inhibitors through total synthesis: lessons from structure-activity studies of (+)-migrastatin J. Am. Chem. Soc. 126 2004 1038 1040
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 1038-1040
    • Njardarson, J.T.1    Gaul, C.2    Shan, D.3    Huang, X.Y.4    Danishefsky, S.J.5
  • 21
    • 4143073625 scopus 로고    scopus 로고
    • Strategy in inhibition of cathepsin B, A target in tumor invasion and metastasis
    • I.T. Lim, S.O. Meroueh, M. Lee, M.J. Heeg, and S. Mobashery Strategy in inhibition of cathepsin B, A target in tumor invasion and metastasis J. Am. Chem. Soc. 126 2004 10271 10277
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 10271-10277
    • Lim, I.T.1    Meroueh, S.O.2    Lee, M.3    Heeg, M.J.4    Mobashery, S.5
  • 22
    • 33746851956 scopus 로고    scopus 로고
    • Tumor metastasis: Mechanistic insights and clinical challenges
    • P.S. Steeg Tumor metastasis: mechanistic insights and clinical challenges Nat. Med. 12 2006 895 904
    • (2006) Nat. Med. , vol.12 , pp. 895-904
    • Steeg, P.S.1
  • 23
  • 24
    • 0001302290 scopus 로고
    • Malyngamide A, a novel chlorinated metabolite of the marine cyanophyte Lyngbya majuscule
    • J.H. Cardellina II, F.J. Marner, and R.E. Moore Malyngamide A, a novel chlorinated metabolite of the marine cyanophyte Lyngbya majuscule J. Am. Chem. Soc. 101 1979 240 242
    • (1979) J. Am. Chem. Soc. , vol.101 , pp. 240-242
    • Cardellina, I.I.J.H.1    Marner, F.J.2    Moore, R.E.3
  • 25
    • 0034526422 scopus 로고    scopus 로고
    • New malyngamides from the Hawaiian cyanobacterium Lyngbya majuscule
    • Y. Kan, B. Sakamoto, T. Fujita, and H. Nagai New malyngamides from the Hawaiian cyanobacterium Lyngbya majuscule J. Nat. Prod. 63 2000 1599 1602
    • (2000) J. Nat. Prod. , vol.63 , pp. 1599-1602
    • Kan, Y.1    Sakamoto, B.2    Fujita, T.3    Nagai, H.4
  • 26
    • 34047205048 scopus 로고    scopus 로고
    • Total synthesis and correct absolute configuration of malyngamide U
    • Y. Li, J.P. Feng, W.H. Wang, J. Chen, and X.P. Cao Total synthesis and correct absolute configuration of malyngamide U J. Org. Chem. 72 2007 2344 2350
    • (2007) J. Org. Chem. , vol.72 , pp. 2344-2350
    • Li, Y.1    Feng, J.P.2    Wang, W.H.3    Chen, J.4    Cao, X.P.5
  • 27
    • 66249139890 scopus 로고    scopus 로고
    • A convergent route for the total synthesis of malyngamides O, P, Q, and R
    • J. Chen, X.G. Fu, L. Zhou, J.T. Zhang, X.L. Qi, and X.P. Cao A convergent route for the total synthesis of malyngamides O, P, Q, and R J. Org. Chem. 74 2009 4149 4157
    • (2009) J. Org. Chem. , vol.74 , pp. 4149-4157
    • Chen, J.1    Fu, X.G.2    Zhou, L.3    Zhang, J.T.4    Qi, X.L.5    Cao, X.P.6
  • 28
    • 0028834846 scopus 로고
    • Malyngamide i and the structure revision of stylocheilamide
    • J.S. Todd, and W.H. Gerwick Malyngamide I and the structure revision of stylocheilamide Tetrahedron Lett. 36 1995 7837 7840
    • (1995) Tetrahedron Lett. , vol.36 , pp. 7837-7840
    • Todd, J.S.1    Gerwick, W.H.2
  • 29
    • 0031909145 scopus 로고    scopus 로고
    • Malyngamides M and N from the hawaiian red alga Gracilaria coronopifolia
    • Y. Kan, T. Fujita, H. Nagai, B. Sakamoto, and Y. Hokama Malyngamides M and N from the hawaiian red alga Gracilaria coronopifolia J. Nat. Prod. 61 1998 152 155
    • (1998) J. Nat. Prod. , vol.61 , pp. 152-155
    • Kan, Y.1    Fujita, T.2    Nagai, H.3    Sakamoto, B.4    Hokama, Y.5
  • 30
    • 0033753789 scopus 로고    scopus 로고
    • Malyngamides O and P from the sea hare Stylocheilus longicauda
    • W.A. Gallimore, and P.J. Scheuer Malyngamides O and P from the sea hare Stylocheilus longicauda J. Nat. Prod. 63 2000 1422 1424
    • (2000) J. Nat. Prod. , vol.63 , pp. 1422-1424
    • Gallimore, W.A.1    Scheuer, P.J.2
  • 32
    • 0001355372 scopus 로고
    • (-)-trans-7(S)-Methoxytetradec-4-enoic acid and related amides from the marine cyanophyte Lyngbya majuscule
    • J.H. Cardellina II, D. Dalietos, F.J. Marner, J.S. Mynderse, and R.E. Moore (-)-trans-7(S)-Methoxytetradec-4-enoic acid and related amides from the marine cyanophyte Lyngbya majuscule Phytochemistry 17 1978 2091 2095
    • (1978) Phytochemistry , vol.17 , pp. 2091-2095
    • Cardellina, I.I.J.H.1    Dalietos, D.2    Marner, F.J.3    Mynderse, J.S.4    Moore, R.E.5
  • 34
    • 5044238876 scopus 로고    scopus 로고
    • Integrin signalling during tumour progression
    • W. Guo, and F.G. Giancotti Integrin signalling during tumour progression Nat. Rev. Mol. Cell. Biol. 5 2004 816 826
    • (2004) Nat. Rev. Mol. Cell. Biol. , vol.5 , pp. 816-826
    • Guo, W.1    Giancotti, F.G.2
  • 35
    • 64049106881 scopus 로고    scopus 로고
    • Integrin signaling and cell spreading alterations by rottlerin treatment of chick limb bud mesenchymal cells
    • Y.A. Choi, D.K. Kim, S.S. Kang, J.K. Sonn, and E.J. Jin Integrin signaling and cell spreading alterations by rottlerin treatment of chick limb bud mesenchymal cells Biochimie 91 2009 624 631
    • (2009) Biochimie , vol.91 , pp. 624-631
    • Choi, Y.A.1    Kim, D.K.2    Kang, S.S.3    Sonn, J.K.4    Jin, E.J.5
  • 37
    • 67651085772 scopus 로고    scopus 로고
    • Signal transduction by focal adhesion kinase in cancer
    • J. Zhao, and J.L. Guan Signal transduction by focal adhesion kinase in cancer Cancer Metastasis Rev. 28 2009 35 49
    • (2009) Cancer Metastasis Rev. , vol.28 , pp. 35-49
    • Zhao, J.1    Guan, J.L.2
  • 38
    • 67649849871 scopus 로고    scopus 로고
    • Integrin beta1-focal adhesion kinase signaling directs the proliferation of metastatic cancer cells disseminated in the lungs
    • T. Shibue, and R.A. Weinberg Integrin beta1-focal adhesion kinase signaling directs the proliferation of metastatic cancer cells disseminated in the lungs Proc. Natl. Acad. Sci. USA 106 2009 10290 10295
    • (2009) Proc. Natl. Acad. Sci. USA , vol.106 , pp. 10290-10295
    • Shibue, T.1    Weinberg, R.A.2
  • 39
    • 33745231161 scopus 로고    scopus 로고
    • Emodin inhibits tumor cell adhesion through disruption of the membrane lipid rafts-associated integrin signaling pathway
    • Q. Huang, H.M. Shen, G. Shui, M.R. Wenk, and C.N. Ong Emodin inhibits tumor cell adhesion through disruption of the membrane lipid rafts-associated integrin signaling pathway Cancer Res. 66 2006 5807 5815
    • (2006) Cancer Res. , vol.66 , pp. 5807-5815
    • Huang, Q.1    Shen, H.M.2    Shui, G.3    Wenk, M.R.4    Ong, C.N.5
  • 40
    • 20844437106 scopus 로고    scopus 로고
    • Glycans in cancer and inflammation - Potential for therapeutics and diagnostics
    • D.H. Dube, and C.R. Bertozzi Glycans in cancer and inflammation - potential for therapeutics and diagnostics Nat. Rev. Drug Discov. 4 2005 477 488
    • (2005) Nat. Rev. Drug Discov. , vol.4 , pp. 477-488
    • Dube, D.H.1    Bertozzi, C.R.2
  • 41
    • 0019489031 scopus 로고
    • Metastatic potential is positively correlated with cell surface sialylation of cultured murine tumor cell lines
    • G. Yogeeswaran, and P.L. Salk Metastatic potential is positively correlated with cell surface sialylation of cultured murine tumor cell lines Science 212 1981 1514 1516
    • (1981) Science , vol.212 , pp. 1514-1516
    • Yogeeswaran, G.1    Salk, P.L.2
  • 42
    • 19644364143 scopus 로고    scopus 로고
    • Hypersialylation of B1 integrins, observed in colon adenocarcinoma, may contribute to cancer progression by up-regulating cell motility
    • E.C. Seales, G.A. Jurado, B.A. Brunson, J.K. Wakefield, A.R. Frost, and S.L. Bellis Hypersialylation of B1 integrins, observed in colon adenocarcinoma, may contribute to cancer progression by up-regulating cell motility Cancer Res. 65 2005 4645 4652
    • (2005) Cancer Res. , vol.65 , pp. 4645-4652
    • Seales, E.C.1    Jurado, G.A.2    Brunson, B.A.3    Wakefield, J.K.4    Frost, A.R.5    Bellis, S.L.6
  • 43
    • 67349087158 scopus 로고    scopus 로고
    • ST6Gal-I expression in ovarian cancer cells promotes an invasive phenotype by altering integrin glycosylation and function
    • D.R. Christie, F.M. Shaikh, J.A. Lucas IV, J.A. Lucas III, and S.L. Bellis ST6Gal-I expression in ovarian cancer cells promotes an invasive phenotype by altering integrin glycosylation and function J. Ovarian Res. 1 2008 3
    • (2008) J. Ovarian Res. , vol.1 , pp. 3
    • Christie, D.R.1    Shaikh, F.M.2    Lucas, I.V.J.A.3    Lucas Iii, J.A.4    Bellis, S.L.5
  • 44
    • 39049137589 scopus 로고    scopus 로고
    • α2-6-linked sialic acids on N-glycans modulate carcinoma differentiation in vivo
    • M. Hedlund, E. Ng, A. Varki, and N.M. Varki α2-6-linked sialic acids on N-glycans modulate carcinoma differentiation in vivo Cancer Res. 68 2008 388 394
    • (2008) Cancer Res. , vol.68 , pp. 388-394
    • Hedlund, M.1    Ng, E.2    Varki, A.3    Varki, N.M.4
  • 46
    • 77950842888 scopus 로고    scopus 로고
    • A novel sialyltransferase inhibitor AL10 suppresses invasion and metastasis of lung cancer cells by inhibiting integrin-mediated signaling
    • C.H. Chiang, C.H. Wang, H.C. Chang, S.V. More, W.S. Li, and W.C. Hung A novel sialyltransferase inhibitor AL10 suppresses invasion and metastasis of lung cancer cells by inhibiting integrin-mediated signaling J. Cell. Physiol. 223 2010 492 499
    • (2010) J. Cell. Physiol. , vol.223 , pp. 492-499
    • Chiang, C.H.1    Wang, C.H.2    Chang, H.C.3    More, S.V.4    Li, W.S.5    Hung, W.C.6
  • 47
    • 33646067143 scopus 로고    scopus 로고
    • Lithocholic acid analogues, new and potent α-2,3-sialyltransferase inhibitors
    • K.H. Chang, L. Lee, J. Chen, and W.S. Li Lithocholic acid analogues, new and potent α-2,3-sialyltransferase inhibitors Chem. Commun. 2006 629 631
    • (2006) Chem. Commun. , pp. 629-631
    • Chang, K.H.1    Lee, L.2    Chen, J.3    Li, W.S.4
  • 48
    • 0021950724 scopus 로고
    • Total synthesis of antibiotic althiomycin
    • K. Inami, and T. Shiba Total synthesis of antibiotic althiomycin Bull. Chem. Soc. Jpn. 58 1985 352 360
    • (1985) Bull. Chem. Soc. Jpn. , vol.58 , pp. 352-360
    • Inami, K.1    Shiba, T.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.